Pilot to Aerospace Engineer?

I'm a rising high school junior and over this summer I've decided that I would like to be a Test Pilot in the Air Force, going through AFROTC. I plan on getting an aerospace engineering degree (possibly mechanical, or both) in college.

Now, the question is what is the feasibility of serving the 7 or so years in the Air Force and then finding a job as an aerospace engineer at somewhere like NASA or a private aerospace company?

Also, what are the possibilities for graduate education while serving as a pilot in the Air Force? On multiple sites it says that you can pursue a degree at the Air Force Institute of Technology, but it doesn't seem that a Masters or Doctorate degree from there holds the same respect as from a higher end civilian university. Can you get money and time to get a Masters/Doctorate from a place like Stanford or MIT while still serving?

If you really want to fly for a living, the Air Force Academy is the way to go.
The engineering degree and pilot license are really things you'll do "on the side" in the big picture. If you do well, you will get lots of multi-engine turbine flight time... something you just don't get on your own (and is inaccessible to the average joe due to it's prohibitively expensive operation costs).

Look up how much multi-engine turbine training costs... it's insane.

I have no military obligation and the freedom of flying when and where I want, but I'm relegated to small piston engine aircraft.

Can you get money and time to get a Masters/Doctorate from a place like Stanford or MIT while still serving?

I don't know about the Air Force, but I know the Navy sends a number of officers to MIT for doctorates. Masters are easier in any branch of service - you get posted as an ROTC instructor and pick up your masters then. I also know that the services are not at all interested in getting someone an advanced degree only to have them leave, so expect an additional commitment.

On multiple sites it says that you can pursue a degree at the Air Force Institute of Technology, but it doesn't seem that a Masters or Doctorate degree from there holds the same respect as from a higher end civilian university.

I'm not sure this is true - it depends on what you're studying (just like anywhere else). To become a test pilot in the Air Force, you would have to attend AFIT and get a degree in Flight Testing (not sure if this is actually what the degree is called). It is a two year program, and when you're done you have a Masters in Flight Testing. The graduation exercise, I believe, is to develop a test plan (presumably for something that needs to be tested) and to carry out the test. This parallels very closely what would be expected for a "normal" masters degree. Test pilots are professional researchers.

I have a close high school friend who attended the Air Force Academy, graduated last year, and is now at pilot school (which I believe is one year long). The commitment to the Air Force for attending the Academy is 7 years, and for attending pilot school, I think it becomes 11 years. I have another friend who took the ROTC route with the Navy and is at their pilot school. His commitment will also be 11 years for having become a pilot.

I have been told that it works something like this: You go to school and participate in the ROTC program for four (or five, depending on your school) years. In your last year, you apply to become a pilot. You have to meet all of the physical requirements (size, health, allergies, eyesight, etc.) and you have to have good grades (it's somewhat competitive). You get accepted into pilot school. After graduation from college you are assigned some kind of desk job while waiting to start pilot school (maybe a year or less). You finally get to go to flight school (about a year, I think). When you graduate, you're a pilot and you're assigned to some base where you get to fly a plane as part of your job (pretty sweet!). After a while (not sure if there's a time requirement on this) you apply to go to AFIT to become a test pilot. I don't know anything about how competitive this is or what the requirements are to do this, but my guess is that it is competitive. You get accepted to do this and you're golden - two more years of school and you're a test pilot. My point here is that you'll really have to work to become a test pilot in the military. Nothing is guaranteed in the military - you're at the mercy of your superiors. Becoming a test pilot is a really good goal, though - Good Luck!

As for finding a job in the civilian world after (if) you leave the service - I doubt that will be a problem. I work for a company that develops flight simulators and we LOVE to hire people with a military background, for both technical and non-technical positions. As a defense contractor, it helps to have employees who know [the right] people in the military and as a company that develops flight simulators, it is invaluable to have someone with experience in the jets that we're trying to simulate. This is only one example, though, and I have to believe that there are many other companies out there in similar situations. And if there aren't companies that are specifically looking for people with military backgrounds, I think an aerospace engineering degree would be in high enough demand that finding a job wouldn't be a problem.